(4S,5R)-5-Allyl-4-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 1053617-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-5-Allyl-4-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5R)-4-(aminomethyl)-2,2-dimethyl-5-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 1053617-11-0
• 化学式: C₁₄H₂₆N₂O₃
• 分子量: 270.372
• InChiKey: BDRXRLPOWSZCND-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸苄酯 、 (4S,5R)-5-Allyl-4-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 tert-butyl (4S,5R)-2,2-dimethyl-4-<<(benzyloxycarbonyl)amino>methyl>-5-(2'-propenyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053
• 作为产物：
  描述：

  (4S,5R)-5-Allyl-4-(2,2-dimethyl-propionyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 氢氧化钾 、 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 55.0h， 生成 (4S,5R)-5-Allyl-4-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053